1999–2000 Dumbarton F.C. season
|Stadium||Boghead Park, Dumbarton|
|Scottish League Division 3||6th|
|Scottish Cup||Second Round|
|Scottish League Cup||First Round|
|Bell's Challenge Cup||First Round|
League: Paddy Flannery (14)|
All: Paddy Flannery (16)
|Highest home attendance||3,031|
|Lowest home attendance||324|
|Average home league attendance||581|
Season 1999–2000 was the 116th football season in which Dumbarton competed at a Scottish national level, entering the Scottish Football League for the 94th time, the Scottish Cup for the 105th time, the Scottish League Cup for the 53rd time and the Scottish Challenge Cup for the ninth time.
Season 1999-2000 would be one of the most memorable for Dumbarton, but not because of any titles won or lost, but because this would be the last season that the club would play at their famous Boghead Park. Dumbarton's home had been here for the past 121 years - the longest that any British football club had stayed at any home ground. Now the ground had been sold and Dumbarton would move to a new purpose built stadium at the foot of Dumbarton Rock.
The season itself was unremarkable. Three promotion places were up for grabs due to the addition of Elgin City and Peterhead the following season, however despite an encouraging start there was never a real chance of a top three finish and in the end a midtable 6th place was achieved. It would be the final game however that would define the whole campaign. As it was a crowd in excess of 3,000 turned out to bid farewell to the old ground and with it a fine victory over promoted East Fife.
In the national cup competitions, there was little to cheer. In the Scottish Cup, Dumbarton lost to Stenhousemuir in the second round.
In the League Cup, after a win over Brechin City, Dundee would easily dispatch Dumbarton in the second round.
With new found sponsorship, the Scottish Challenge Cup was re-instated, but the same old failures beset Dumbarton - yet another first round defeat, this time to Airdrie.
Locally, in the Stirlingshire Cup, Dumbarton lost their two group ties.
All results are written with Dumbarton's score first.
|7 August 1999||Albion Rovers||A||3-1||King;Melvin(2)||308|
|14 August 1999||Montrose||H||3-4||Flannery(2);Brown||436|
|21 August 1999||East Fife||A||0-1||591|
|28 August 1999||Brechin City||A||2-0||King;Flannery||357|
|4 September 1999||Berwick Rangers||H||2-1||Flannery;Robertson||324|
|11 September 1999||Queen's Park||H||0-1||539|
|18 September 1999||East Stirling||A||3-1||Templeman(3)||284|
|25 September 1999||Cowdenbeath||H||1-1||Robertson||424|
|2 October 1999||Forfar Athletic||A||0-5||397|
|16 October 1999||Montrose||A||4-1||Grace;Flannery;Smith(2)||274|
|23 October 1999||Albion Rovers||H||1-1||Smith||590|
|30 October 1999||Queen's Park||A||2-3||Ward;Bradford||713|
|6 November 1999||East Stirling||H||1-0||Bradford||415|
|14 November 1999||Berwick Rangers||H||1-0||Bradford||415|
|20 November 1999||Brechin City||H||1-3||Flannery||447|
|27 November 1999||Forfar Athletic||H||3-3||Flannery;Robertson;Stewart||469|
|8 December 1999||Cowdenbeath||A||2-0||Brown;Robertson||262|
|18 December 1999||Albion Rovers||A||0-3||257|
|3 January 2000||East Stirling||A||1-2||Flannery||308|
|22 January 2000||Cowdenbeath||H||2-0||Flannery;Brown||469|
|29 January 2000||Queen's Park||H||1-1||Flannery||492|
|5 February 2000||Forfar Athletic||H||3-4||Flannery;Robertson;Smith||439|
|12 February 2000||Brechin City||A||2-1||Flannery;Brown||278|
|26 February 2000||Montrose||H||3-2||King;Robertson;Hringsson||482|
|4 March 2000||East Fife||A||1-2||Watters||436|
|11 March 2000||Queen's Park||A||0-2||788|
|14 March 2000||Berwick Rangers||H||0-2||330|
|18 March 2000||East Stirling||H||3-0||Dillon;Hringsson;Watters||367|
|25 March 2000||Brechin City||H||2-1||Brittain;Grace||365|
|28 March 2000||East Fife||H||1-1||Hringsson||394|
|1 April 2000||Berwick Rangers||H||0-0||560|
|8 April 2000||Cowdenbeath||A||2-1||Flannery(2)||284|
|15 April 2000||Forfar Athletic||H||0-0||474|
|22 April 2000||Albion Rovers||H||0-0||415|
|29 April 2000||Montrose||A||1-2||King||267|
|6 May 2000||East Fife||H||2-1||King;Robertson||3,031|
|8 January 2000||2||Stenhousemuir||H||0-2||302|
Scottish League Cup
|31 July 1999||1||Brechin City||A||2-0||Flannery(2)||346|
|17 August 1999||2||Dundee||A||0-4||2,765|
Bell's Challenge Cup
|10 August 1999||1||Airdrie||A||1-2||Dillon||826|
|14 July 1999||P||Stirling Albion||A||0-3|
|17 July 1999||P||Alloa Athletic||H||2-3||King;Brown||118|
|27 July 1999||Kilmarnock||H||2-6||King;Gow|
|No.||Pos||Nat||Player||Total||Third Division||League Cup||Challenge Cup||Scottish Cup|
Dumbarton played an under 19 team in the Scottish Youth Division B, and with 6 wins and 4 draws from 26 games, finished 9th of 10.
* The League match against Albion Rovers on 8 August marked Kenny Meechan's 100th appearance for Dumbarton in all national competitions - the 114th Dumbarton player to reach this milestone.
- Scottish Football League Review 2000-01. The Scottish Football League. 2001.
- McAllister, Jim (2002). The Sons of the Rock - The Official History of Dumbarton Football Club. Dumbarton: J&J Robertson Printers.
- Litster, John. Record of Post-War Scottish League Players. Norwich: PM Publications.
- Derek Barnes (Dumbarton Football Club Historical Archive)
- Paul Finnegan (Dumbarton Football Club Historical Archive)
- Alan Brown (Dumbarton Football Club Historical Archive)
- Hrienn Hringsson (Dumbarton Football Club Historical Archive)
- Chris Smith (Dumbarton Football Club Historical Archive)
- Scottish Football Historical Archive